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Literature summary extracted from

  • Köllner, T.G.; Schnee, C.; Li, S.; Svatos, A.; Schneider, B.; Gershenzon, J.; Degenhardt, J.
    Protonation of a neutral (S)-beta-bisabolene intermediate is involved in (S)-beta-macrocarpene formation by the maize sesquiterpene synthases TPS6 and TPS11 (2008), J. Biol. Chem., 283, 20779-20788.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.55 overexpression in Escherichia coli Zea mays
5.5.1.17 expressed in Escherichia coli Top10 cells Zea mays
5.5.1.17 overexpression in Escherichia coli Zea mays

Protein Variants

EC Number Protein Variants Comment Organism
4.2.3.55 D526N mutation inactivates the enzyme completely Zea mays
4.2.3.55 Y522F mutation reduces the production of (S)-beta-macrocarpene to trace amounts, the enzyme forms (S)-beta-bisabolene almost exclusively, the overall activity of the mutated enzyme is dramatically reduced Zea mays
5.5.1.17 D526N inactive Zea mays
5.5.1.17 D526N mutation inactivates the enzyme completely Zea mays
5.5.1.17 Y522F the mutation strongly reduces the rate of reprotonation of (S)-beta-bisabolene Zea mays

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
4.2.3.55 0.0021
-
 (2E,6E)-farnesyl diphosphate 30°C Zea mays
5.5.1.17 0.0011
-
 geranyl diphosphate recombinant enzyme, in the presence of 0.05 mM Mn2+, pH and temperature not specified in the publication Zea mays

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
4.2.3.55 cytoplasm
-
 Zea mays 5737
-
5.5.1.17 cytoplasm
-
 Zea mays 5737
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.55 Mg2+ TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mg2+ measured with 0.01 mM farnesyl diphosphate: 0.131 mM Zea mays
4.2.3.55 Mn2+ TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mn2+ measured with 0.01 mM farnesyl diphosphate: 0.0234 mM Zea mays
5.5.1.17 Mg2+ TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta-bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mg2+ measured with 0.01 mM farnesyl diphosphate: 0.131 mM Zea mays
5.5.1.17 Mg2+ the enzyme is mostly stimulated by 10 mM Mg2+ Zea mays
5.5.1.17 Mn2+ TPS6 requires a divalent metal ion, with Mg2+ and Mn2+ being effective, optimum activity with 5 mM Mg2+ and 5 mM Mn2+. Although the Km for Mn2+ is significantly lower than for Mg2+, the enzyme is more likely to operate with a Mg2+ cofactor in planta, because the concentration of Mg2+ in plant cells is about 2 orders of magnitudes higher than Mn2+. In the presence of Mn2+, the product spectrum of TPS6 is shifted toward an increased production of (S)-beta-bisabolene and a decreased production of (S)-beta-macrocarpene. KM-value for Mn2+ measured with 0.01 mM farnesyl diphosphate: 0.0234 mM Zea mays
5.5.1.17 Mn2+ the enzyme is stimulated by 0.25 mM Mn2+. In the presence of Mn2+, there is increased formation of (S)-beta-bisabolene Zea mays
5.5.1.17 additional information no stimulation of activity is observed in the presence of Ca2+, Cd2+, Co2+, Cu2+, Ni2+, and Zn2+ (0.25 and 5 mM each) Zea mays

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.55 (2E,6E)-farnesyl diphosphate Zea mays the enzyme may be involved in plant defense (S)-beta-bisabolene + diphosphate
-
 ?
4.2.3.55 (2E,6E)-farnesyl diphosphate Zea mays the enzyme may be involved in plant defense (S)-beta-bisabolene + diphosphate i.e. ((4S)-1-methyl-4-(5-methyl-1-methylidenehex-4-en-1-yl)cyclohexene ?
5.5.1.17 (S)-beta-bisabolene Zea mays the enzyme may be involved in plant defense (S)-beta-macrocarpene
-
 ?
5.5.1.17 (S)-beta-bisabolene Zea mays the enzyme may be involved in plant defense (S)-beta-macrocarpene i.e. (1'S)-4',5,5-trimethyl-1,1'-bi(cyclohexane)-1,3'-diene. Product is identified by GC-MS ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.55 Zea mays Q1EG72 L. variety B73
-
4.2.3.55 Zea mays Q5GJ60 L. variety B73
-
5.5.1.17 Zea mays Q1EG72 variety B73
-
5.5.1.17 Zea mays Q1EG72 L. variety B73
-
5.5.1.17 Zea mays Q5GJ60 variety B73
-
5.5.1.17 Zea mays Q5GJ60 L. variety B73
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.3.55 partial Zea mays
5.5.1.17 partial Zea mays
5.5.1.17 partial purification Zea mays

Reaction

EC Number Reaction Comment Organism Reaction ID
4.2.3.55 (2E,6E)-farnesyl diphosphate = (S)-beta-bisabolene + diphosphate (S)-beta-bisabolene is a stable intermediate. (S)-beta-Macrocarpene formation requires a protonation of the intermediate Zea mays
a
4.2.3.55 (2E,6E)-farnesyl diphosphate = (S)-beta-bisabolene + diphosphate The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second steps is the isomerization to (S)-beta-macrocarpene (c.f. EC 5.5.1.a, (S)-beta-macrocarpene synthase). The enzyme requires Mg2+ or Mn2+ for activity. Zea mays
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
4.2.3.55 root the enzyme is predominantly active in the roots Zea mays
-
5.5.1.17 leaf
-
 Zea mays
-
5.5.1.17 root
-
 Zea mays
-
5.5.1.17 root the enzyme is predominantly active in the roots Zea mays
-
5.5.1.17 seedling
-
 Zea mays
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.55 (2E,6E)-farnesyl diphosphate
-
 Zea mays (S)-beta-bisabolene + diphosphate The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS ?
4.2.3.55 (2E,6E)-farnesyl diphosphate the enzyme may be involved in plant defense Zea mays (S)-beta-bisabolene + diphosphate
-
 ?
4.2.3.55 (2E,6E)-farnesyl diphosphate the enzyme may be involved in plant defense Zea mays (S)-beta-bisabolene + diphosphate i.e. ((4S)-1-methyl-4-(5-methyl-1-methylidenehex-4-en-1-yl)cyclohexene ?
4.2.3.55 (2Z,6E)-farnesyl diphosphate
-
 Zea mays (S)-beta-bisabolene + diphosphate The synthesis of (S)-beta-macrocarpene from (2E,6E)-farnesyl diphosphate proceeds in two steps. The first step is the cyclization to (S)-beta-bisabolene. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase). Product is identified by GC-MS ?
4.2.3.55 additional information no activity with geranylgeranyl diphosphate. TPS6 accepts the monoterpene precursor geranyl diphosphate but the monoterpene products are produced at a lower velocity Zea mays ?
-
 ?
5.5.1.17 (S)-beta-bisabolene
-
 Zea mays (S)-beta-macrocarpene i.e. (1'S)-4',5,5-trimethyl-1,1'-bi(cyclohexane)-1,3'-diene. Product is identified by GC-MS ?
5.5.1.17 (S)-beta-bisabolene the enzyme may be involved in plant defense Zea mays (S)-beta-macrocarpene
-
 ?
5.5.1.17 (S)-beta-bisabolene the enzyme may be involved in plant defense Zea mays (S)-beta-macrocarpene i.e. (1'S)-4',5,5-trimethyl-1,1'-bi(cyclohexane)-1,3'-diene. Product is identified by GC-MS ?
5.5.1.17 (S)-beta-bisabolene the synthesis of (S)-macrocarpene from (2E,6E)-farnesyl diphosphate in two steps. The first step is the cyclization to (S)-beta-. The second step is the isomerization to (S)-beta-macrocarpene ((S)-beta-macrocarpene synthase) Zea mays (S)-beta-macrocarpene i.e. (1'S)-4',5,5-trimethyl-1,1'-bi(cyclohexane)-1,3'-diene. Product is identified by GC-MS ?
5.5.1.17 (S)-beta-bisabolene (S)-beta-macrocarpene formation by TPS11 requires a protonation of the (S)-beta-bisabolene intermediate Zea mays (S)-beta-macrocarpene
-
 ?
5.5.1.17 geranyl diphosphate
-
 Zea mays (S)-beta-bisabolene + (S)-beta-macrocarpene in the presence of geranylgeranyl diphosphate, TPS11 also catalyzes the formation of beta-myrcene and linalool, along with minor amounts of limonene, alpha-thujene, sabinene, and alpha-terpinolene ?
5.5.1.17 additional information no enzymatic activity is observed in the presence of geranylgeranyl diphosphate Zea mays ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.55 TPS11
-
 Zea mays
4.2.3.55 TPS6
-
 Zea mays
5.5.1.17 TPS11
-
 Zea mays
5.5.1.17 TPS6
-
 Zea mays

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.3.55 30
-
 assay at Zea mays
5.5.1.17 30
-
 assay at Zea mays

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.3.55 7
-
 in presence of 5 mM Mg2+ Zea mays
5.5.1.17 7
-
 in presence of 5 mM Mg2+ Zea mays
5.5.1.17 7
-
 forming beta-macrocarpene Zea mays
5.5.1.17 8.5
-
 forming beta-bisabolene Zea mays

pH Range

EC Number pH Minimum pH Maximum Comment Organism
4.2.3.55 6.2 8.6 half-maximal activity at pH 6.2 and at pH 8.6, in presence of 5 mM Mg2+. Within a pH range from 5.0 to 8.0, the major product is (S)-beta-macrocarpene, but higher pH values favor the formation of (S)-beta-bisabolene Zea mays
5.5.1.17 6.2 8.6 half-maximal activity at pH 6.2 and at pH 8.6, in presence of 5 mM Mg2+. Within a pH range from 5.0 to 8.0, the major product is (S)-beta-macrocarpene, but higher pH values favor the formation of (S)-beta-bisabolene Zea mays

Expression

EC Number Organism Comment Expression
5.5.1.17 Zea mays after leaf damage by Spodoptera littoralis, the transcript level of TSP11 is elevated up
5.5.1.17 Zea mays after leaf damage by Spodoptera littoralis, the transcript level of TSP6 is elevated up

General Information

EC Number General Information Comment Organism
4.2.3.55 physiological function the enzyme may be involved in plant defense Zea mays
5.5.1.17 physiological function the enzyme may be involved in plant defense Zea mays